A Friday series exploring Startups and the people who make them go. Read all If the Shoe Fits posts here

Yesterday we looked at the bootstrapped success of Tuft & Needle and before that at bootstrapping serial entrepreneur Andrew Wilkinson.

All very successful sans venture money.

Sure, thousands of bootstrapped companies fail, as do hundreds of funded companies; some go with a bang and others with barely a whimper.

But a few provide a cautionary tale for both founders and investors.

Lucas Duplan’s Clinkle is one such tale

Clinkle was supposed to be what Apple Pay is today.

In what is termed a “party round” 22 year-old Duplan raised $25 million dollars, mostly in convertible notes, from high profile investors, including Richard Branson, Peter Thiel and Marc Benioff, as well as VCs Accel Partners, Index Ventures and Andreessen Horowitz.

“In a typical party round, no single investor cares enough to think about the company multiple times a day,” wrote Y Combinator President Sam Altman in a June 2013 blog post. “Each investor assumes that at least 1 of the N other investors will be closely involved, but in fact no one is, and the companies sometimes wander off into a very unfocused wilderness.”

However, in the 5 years since founding, 3 since funding, the company has done nothing, gone nowhere and in an almost unheard of action investors are asking for their money back.

Clinkle had a polished demo that came before things like Apple Pay, said one former employee, who declined to be named. But most importantly that person added, Duplan “was charismatic when he wanted to be” and could “raise money in absurd abundance.”

“It was his one skill,” they said. (Emphasis mine.)

The takeaway is beware of great stories, charm and party rounds where the person at the helm has never sailed a boat.

Knowing the correct names of the equipment doesn’t mean a person knows how to use it in the real world or in what order.

Image credit: HikingArtist